Pretty Winchester
by DeansUnicorn1991
Summary: Castiel is a successful businessman, but he's always felt as if something was missing from his life. One night, upon leaving a lavish party in a friend's borrowed car, he becomes lost on the way back to his hotel. Desperate for help, he pulls up alongside the curb of a bustling street to be approached by a green-eyed stranger. Enter Dean Winchester. (loosely based on Pretty Woman)


Pretty Winchester

Chapter 1:

 _This is utterly exhausting,_ thought Castiel as he meandered his way throughout the crowd of cutthroat lawyers and their insipid groupies. Everything and everyone inside Crowley's ridiculous excuse of a home reeked of desperation, greed and an inordinate amount of (dare he say) _sinful_ pride. None of it appealed to the simple taste he had when it came to home décor.

Delicate paintings of intricate honeycomb patterns, lightly fragranced candles of musk and honey and a few monochromatic vases filled with pale honeysuckle were the staples of interior decorating within Castiel's penthouse apartment in his home city of New York. Sure, he had furniture but it was simply function at its finest. A few chairs and a sofa for sitting (not that he required more than one as he never had company) and a coffee table for the sparse home gardening and bee keeping magazines that he would probably never put to use but nonetheless spent countless hours mentally forming in his imagination. _Oh, how he would love to have a garden to tend_ , he internally sighed yet again.

Snapping himself back to reality, he resumed his search of his (sometimes) friend, Crowley. Castiel had had enough of this social gathering and was ready to return to his penthouse suite in one of the best hotels of Beverly Hills. However, he was stuck unless he was able to obtain a ride back into the hustle and bustle of the city.

Surrounded by a group of perfectly plastic women (and a few men) Crowley laughed at what appeared to be a rather crass joke involving a pizza delivery man. Castiel barely managed in everyday life due to a certain amount of social awkwardness that probably stemmed from the extremely repressed and confined childhood he had been forced to lead.

Finally noticing him as he stood quietly detached from the group, Crowley approached him and slung an arm across his shoulders. "Having fun yet Castiel? Or, is your head still in the clouds? Come, come, have a look around. So many beautiful women around, likely drunk and waiting for just the right handsome, blue-eyed, successful businessman to come up and sweep them off of their feet! What's your craving tonight? Something spicy" Crowley gestured to a group of caramel-skinned, radiantly beautiful Hispanic women chatting excitedly over near the open patio area towards the back of the house.

"Or perhaps something a bit milder?" The Irishman tilted his head in the direction of a few, whip-thin generic looking supermodels. Dark hair, svelte figures and half-starved expressions on their faces.

Castiel began to fidget uncomfortably under the keen gaze of Crowley. _He can't possibly know. There's no possible way I've given myself up!_ Castiel thought as he avoided Crowley's stare.

"Or perhaps they're not quite your type? Maybe I'm under the wrong assumption here? I do know a couple of fine young gentlemen that can do amazing things with their mou-"

"Can I borrow your vehicle?" Castiel blurted the question in an effort to stave off the inquiries he wasn't quite ready for.

"My car? What the bloody hell do you want with my car? Can you even drive?" Crowley asked, completely sidetracked by the random question.

"Of course I can drive." Castiel answered the shorter man, puzzled. "Why on Earth would you think I couldn't?"

Crowley shrugged deeply. "Probably because anytime I see you arrive or depart somewhere you climb into or out of a bloody limousine."

"No, I have maintained my knowledge of how to operate a vehicle despite my habit of riding in limousines." Castiel defended himself, somewhat offended. _Motorized vehicles can be operated by teenagers, so I think I'm perfectly capable of handling one myself!_ Castiel thought as he waited while Crowley had some sort of internal debate on whether or not to hand over the set of keys.

Finally, after fishing around in an inner pocket of his suit jacket, Crowley's hand emerged with a simple key attached to a battery operated fob. There appeared to be an insignia of a rearing equestrian on the fob. Castiel had no idea what manner of car the keys belonged to but he was keen to remove himself from this social gathering.

"Be careful with Juliet, her clutch can be a bit touchy with an unpracticed hand." Crowley gazed at Castiel sternly until he received a reverent nod from Castiel and a solemn, "Of course."

Castiel had no idea why the vehicle had a gender and why her name was Juliet, but he wanted to leave as soon as possible. He turned towards the entrance to the house and once outside approached a valet.

It appeared this one was pushing the boundaries of Crowley's steadfast dress code policy for employees. Normally, this uniform consisted of a pair of tailored black slacks with a crisp crease down the front of the leg and a wrinkleless white button-down with a thin red tie and sensible shoes. This valet screamed **man-eater** in a black pleated inappropriate-length skirt, fishnet stockings, 4" pumps and the white button down - tied at the waist - _unbuttoned_ to expose an inordinate amount of cleavage.

"Going somewhere Clarence?" asked a sultry voice. Once Castiel was able to lift his gaze from the wholly inappropriate (yet somewhat endearing) attire, he realized that the young woman who had spoken displayed a name badge on her left breast. **Meg**.

"Um, yes, uh, I'll be needing Crowley's car, um…Meg." Castiel stammered somewhat frustrated.

"With talk like that I think I can help you find a lot more than a car" Meg purred, slinking up to Castiel with a sway in her step. She lightly grasped the tie he was wearing and wound it around her hand, reeling Castiel in until their faces were inches apart.

Castiel blushed crimson and stated, "Just the car please ma'am."

Meg leaned in and seemed to look directly into his soul. _But of course that's impossible,_ thought Castiel as he tried to look away.

Seemingly surprised, Meg leaned back with a gasp. "You really mean that, don't you?"

Unsure how else to answer, Castiel simply nodded.

"Wow, didn't peg you for the type Clarence," Meg stated as she took a step back and raised a hand gently to his face. "Well whenever you find the one, he'll be a lucky guy." Meg smiled gently as she plucked the keys out of Castiel's hand and strode off to ready the car.

"Wait, how did you-?" Castiel began. Meg simply looked over her shoulder and winked at him.

"I'll be right back with Juliet, Clarence. Sit tight." She continued down a smaller offshoot of the winding drive towards a separate building, whistling a familiar but nameless tune.

Castiel stood in silence and scratched his head. _What a strange interaction…_ he thought as a rumble sounded in the distance.

Pulling out his phone from the interior pocket of his jacket, Castiel opened a GPS application and plugged in the address to his hotel. _30 minutes?_ He thought smiling softly, _No problem!_


End file.
